Picture Perfect

Woodstock, Vermont, owes its appeal as much to the legacy of its residents as to its natural setting

It’s possible to feel a trifle uneasy in the seductive presence of Woodstock, Vermont. “Woodstock is Hollywood’s image of Vermont,” the mayor of a less favored nearby community said recently. “The most perfect town in the Green Mountain State,” I learned from a travel magazine. And why shouldn’t it be? one might ask. The town at first seems like a carefully groomed wealthy woman who is strikingly beautiful simply because of all the money that went into her making. But you’ll soon discover there’s more to her than mere glamour.

Located in the central part of the state, with the area’s only east-west artery, Route 4, muscling straight through the town, Woodstock offers enough traffic to bring one back to reality from time to time. But its own reality—virtually undistilled beauty—is what grabbed and kept my attention from my first sight of the place.

On a late spring day, lilac perfumes the air along Pleasant Street, and a church bell, one of five in Woodstock cast by Paul Revere and his sons, chimes the hour. Partway down the street, drawn by the sight of the gleaming white Congregational Church, its spire and pediment of Federal perfection, I arrive at a small bridge, one of many that lace the town together, crossing its two felicitous waterways, Kedron Brook and the Ottauquechee River. To the immediate north of town, and eminently walkable, rises the 2,040-foot Mount Tom, thickly wooded with pine and larch.

It is this friendly intrusion of the natural landscape into the heart of town that is so characteristic of life here. “We must not forget what nature has done for Woodstock, without our help,” wrote the historian Henry Swan Dana in 1881. “We may well say, ‘Our lines have fallen to us in pleasant places, and we have a goodly heritage. . . .’”

This goodly heritage (along with reputed reverses in love) drew the first settler, Timothy Knox. In 1765 he built a small hut and lived for three years as the sole inhabitant of his forest clearing, sustaining himself from the abundant bounty of the woods and rivers. Soon other homesteaders began to trickle in, and by 1771 the census counted forty-two people. In those years the region, first held as a royal charter, was vigorously contested by New Hampshire and New York. In 1777 Vermont became an independent republic, and it finally joined the Union in 1791.

By then Woodstock had been named a shire town, meaning that court was set up there, bringing in judges, lawyers, and jurors. The attendant services, shops, an inn, a state bank, and improved roads and bridges followed. Small factories grew up along the water, and local craftsmen and artisans—R. H. Bailey, the silversmith, John White, the chair-maker—found plenty of business. On Pleasant Street, hard by the rushing Kedron Brook, stood a sawmill. The barrel maker, printer, and potter also set up shop adjacent to their homes here, and though the street is now mostly residential, hints remain of the original purposes of its structures.

On Elm Street, which runs perpendicular to Pleasant, the town’s most impressive houses rose. Starting around 1800, they were the work of professional architects who more than met the aspirations of their clients. The legislators and lawyers resided in spacious colonnaded houses of brick or clapboard, fronted by strict picket fences and backed by immense lawns that flow down to the river. Like much of present-day Woodstock, these Elm Street beauties wear their two hundred years lightly. One of them, the 1807 Dana House, now functions as the Woodstock Historical Society. Guided tours of the house provide an excellent way to see how the town fathers and their families lived as the village grew into its grandest self.

Certain family names—Dana, Marsh, Billings, and, from the 1930s on, Rockefeller—are woven into Woodstock’s fabric. Without them it might have turned out to be a very different place. Charles Dana, an early merchant, built the house that is now the historical society. In 1889 his son Henry published a history of Woodstock that is still considered a model of its kind. This volume was commissioned by Frederick Billings, who arrived in Woodstock at the age of twelve as the son of a destitute farmer.

Billings’s first view of Woodstock came as he was herding a pig into town, part of the remaining holdings of his debtor father, who had been ordered to live there, close to the jail. “The pig gave out near the village,” writes Peter Jennison in his history of Woodstock. “It was the lowest point of Frederick’s life and he vowed he would never be poor again.” In any event Billings found kind treatment in the town, and later, when he grew immensely wealthy from mining and railroad ventures in the West, he gave back these kindnesses many times over. In 1869 he bought and refurbished the homestead of George Perkins Marsh, a Woodstock native, scholar, and diplomat and, most significantly, the founder of America’s (and very likely the world’s) modern conservation movement. After Marsh’s death Billings also purchased his twelve-thousand-volume library and donated $250,000 to the University of Vermont for a building to house it.